Vacation rentals with a patio in West Side

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Top-rated patio rentals in West Side

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Guest favorite

Apartment in Forest Park

4.99 out of 5 average rating, 90 reviews

Sunny 1 bedroom apartment 1 block from restaurants

This sunny second floor apartment perched in an 1890’s farmhouse offers traditional charm with many contemporary touches. It showcases a variety of original art. Located on a quiet street but just steps away from restaurants, bars and shops, off-street parking is included. Two nearby trains provide easy access to downtown Chicago and O’Hare Airport. An enclosed porch directly off the kitchen overlooks a beautiful prairie garden. You can relax on the backyard patio with gas grill and fire pit.

Feb 23 – Mar 2

R2,247 ZAR per night

Guest favorite

Apartment in Oak Park

4.91 out of 5 average rating, 104 reviews

Lovely, spacious 2bd, 1bath home w/free parking

Bring the whole family to enjoy this great place with lots of comforts and space. Beautifully decorated with reclaimed barn wood throughout the home and a completely remodeled kitchen with cute bistro table to enjoy your coffee. Wonder around this beautiful, quiet Frank Lloyd Wright neighborhood to see beautiful Victorian homes and architect or take a brisk walk to downtown Oak Park before taking in the sites in Downtown Chicago. Whether you stay for a while or a few days, welcome home!

Sep 13 – 20

R2,419 ZAR per night

Guest favorite

Guest suite in Chicago

4.94 out of 5 average rating, 51 reviews

Logan Square’s Garden apt style rental

It’s an “in-law”apt (the unit) in the bsmt. Entry w/ lockbox for the front gate.key, security-outdoor cameras. The door to the unit is keypad entry. Access to main house through indoors-locked. Free Street pkg. Full bath. 1 BR w/a NEW queen bed frame- no more squeakiness! Living area w/a pull-out couch (queen). Also, a futon that lays out if. Full kitchen& laundry Outdoor space &yard. In season I have 4 garden beds w/a variety that you can help yourself to. Pets need to be on the booking

Feb 11 – 18

R2,776 ZAR per night

Guest favorite

Condo in Chicago

4.96 out of 5 average rating, 120 reviews

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Jun 14 – 21

R5,464 ZAR per night

Superhost

Apartment in Chicago

4.78 out of 5 average rating, 18 reviews

Sunny garden apartment in West Logan Square

Full of unique art and bright colors, you'll find yourself quite comfortable in our garden apartment in Logan Square. Bedroom has a comfy queen-sized bed and living room couch is also a twin bed. Full kitchen and bath, with all the basics. Gorgeous outdoor space, with a perennial garden and private dining area. Steps from the 606, Humboldt Park, and all the joys of Logan Square! We live in the home, so you may hear the sounds of our two kids at times, but your space has a private entry.

Mar 29 – Apr 5

R2,158 ZAR per night

Guest favorite

Apartment in Berwyn

4.87 out of 5 average rating, 137 reviews

The Green Bungalow: Charming 1-BR apt. with patio

Situated in a residential neighborhood just outside the city limits, this lovely 2nd floor apartment is blocks from the Blue Line train and highway. Our newly renovated vintage unit has a full kitchen, hardwood floors, plenty of natural light, a backyard patio and its own private entrance. Our bungalow is walking distance to cafes, restaurants, shopping, music and nightlife. Enjoy the charm of the suburbs while having easy access to all the attractions Chicago's downtown has to offer.

Jul 24 – 31

R1,988 ZAR per night

Guest favorite

Apartment in Oak Park

4.98 out of 5 average rating, 66 reviews

Cheerful Oak Park Apartment

Welcome to our lovely space, located above a unique piano restoration shop. Spacious and relaxing, with plenty to enjoy staying in, and 5-minutes walking distance to cafes, grocery, bars, restaurants, and more. The apartment is down the street from a Botanic Garden, and there is a nice arts district nearby. Easily accessible to downtown Oak Park and Chicago with nearby public transportation and expressway (downtown Chicago is about 25-35 min. drive, 35-45 min. by train).

Sep 7 – 14

R2,691 ZAR per night

Guest favorite

Apartment in Illinois Medical District

4.93 out of 5 average rating, 14 reviews

Claremont Cottage Tri-Taylor/UIC/UnitedCenter

Beautifully furnished garden apartment in trendy Tri-Taylor neighborhood near United Center & UIC; 2 BR, 1 Full Bath, Fully-Equipped Kitchen, Living/Dining Room, Patio, Lovely Garden. Walk or bike to United Center, UIC, Little Italy, Illinois Med District; 7 min to West Loop, Pilsen, and Chinatown; 15 min to Downtown, Grant Park, our beautiful Lake Shore, and much more! Amenities: WiFi, 3 SmartTVs, Central Heat/Air, Touchscreen Smart Locks w/ personal/private passcode.

Oct 21 – 28

R2,581 ZAR per night

Guest favorite

Apartment in Chicago

4.83 out of 5 average rating, 211 reviews

Cozy Lincoln Park Studio - Steps to Zoo!

This cozy studio in the heart of Lincoln Park is just steps away from some of the best experiences that Chicago has to offer! Just a block from the Lincoln Park Zoo and near the great restaurants and bars of the neighborhood, there's something here for everyone. See a show at the world-famous Second City, take a quick ride up Clark St to see the Cubs play at historic Wrigley Field, or just stay in and relax, there's no wrong way to spend your time in the Windy City!

Nov 18 – 25

R2,976 ZAR per night

Guest favorite

Apartment in Chicago

4.97 out of 5 average rating, 32 reviews

Serene Escape with King Sleep Number Bed, No Fees!

Welcome to our meticulously designed oasis! Relax in luxury on a king-sized Sleep Number bed, refresh in the marbled bathroom with a rain shower, and indulge your culinary passions in the farmhouse-inspired chef's kitchen. Bright, airy, and inviting, our space offers a serene escape. Conveniently located near Belmont CTA Blue Line Station and bus stops, it's the perfect base for your Chicago adventure. Book now for sophistication and comfort!

Mar 27 – Apr 3

R2,332 ZAR per night

Guest favorite

Apartment in Cicero

4.98 out of 5 average rating, 202 reviews

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Quiet city side street. Walking distance to dozens of restaurants and stores. Walking distance to Public Transportation including Metra train, CTA Pink line, Direct CTA Bus to Midway Airport. You will be a short 20-minute drive to Downtown Chicago, 15 minutes to United Center or Soldier Field. Perfect for the quick getaway, the night before your flight, or even the long work assignment. Relax on the Patio with a fire pit and grill.

Feb 25 – Mar 4

R2,363 ZAR per night

Guest favorite

Guest suite in Wheaton

4.85 out of 5 average rating, 103 reviews

Cozy Wheaton Home

Cozy lower level apartment close to DT Wheaton & Glen Ellyn, restaurants, coffee shops, and shopping. Only 40 minutes outside of the DT Chicago! Train station is walking distance. You'll have the entire lower level of our home to yourself! You'll be able to enjoy your own private entrance, living space, and parking . There is everything you need, coffee, tea, mini fridge, microwave, and a comfy couch with a Firestick TV!

Jan 16 – 23

R2,124 ZAR per night